1. Field of the Invention
The present invention relates to novel and valuable diaza bicyclo-(3,3,1)-nonane compounds, to processes of producing such compounds, to pharmaceutical compositions containing diaza bicyclo-(3,3,1)-nonane compounds and their pharmaceutically acceptable acid addition salts, to processes of making such pharmaceutical compositions, and to methods of using said compositions in therapy.
2. The Prior Art
3,7-Diaza bicyclo-(3,3,1)-nonane compounds have become of considerable interest in chemical as well as in pharmacological respect. The chemistry of said compounds is described, for instance, in the following publications:
Russian, Chem. Rev. vol. 34, page 439 (1965); PA0 Ann. Ist. Super Sanita, vol. 4, page 157 (1968); PA0 J. Org. Chem. vol. 33, page 355 (1968) PA0 Russian, Chem. Rev. vol. 42, page 190 (1973); PA0 Chem. Ber. vol. 110, page 3894; PA0 Austral. J. Chem. vol. 13, page 129 (1960); PA0 J. Chem. Soc. vol. 115, page 686 (1919); PA0 Eur. J. med. chem. 1977, pages 301-305. PA0 The pharmacological properties of the known compounds extend from a relatively low local anesthetic activity as described in J. Chem. Soc. 1951, page 1706; PA0 and an effect on the central nervous system as described in Published German Applications No. 26 58 558 and No. 27 49 584, up to a noteworthy antiarrhythmic activity as described in Published German Applications No. 24 28 792; No. 27 26 571, and No. 27 44 248. PA0 Z.sub.1 and Z.sub.2 each denotes hydrogen, or both together form an oxygen while PA0 R.sub.1 and R.sub.2 denote hydrogen, alkyl, alkenyl, or alkinyl, and PA0 R.sub.3 and R.sub.4 each denote an alkyl group, or both together form an alkylene group. PA0 N-Isopropyl-N'-(2-methyl propyl)-9,9-pentamethylene-, PA0 N-Isopropyl-N'-(cyclohexyl)-methyl-9,9-di-n-butyl-, PA0 N-n-Butyl-N'-(2-methyl propyl)-9,9-dimethyl-, PA0 N-n-Butyl-N'-(cyclohexyl)-methyl-9,9-dimethyl-, PA0 N-n-Hexyl-N'-methyl-9,9-diethyl-, PA0 N-(2-Methyl propyl)-N'-(3-butenyl)-9,9-di-n-propyl-, PA0 N-n-butyl-N'-(3-butenyl)-9,9-dimethyl-. PA0 N,N'-Diethyl-9,9-dimethyl-, PA0 N,N'-Di-n-propyl-9,9-diethyl-, PA0 N,N'-Di-isopropyl-9,9-dimethyl-, PA0 N,N'-Di-isopropyl-9,9-di-n-propyl-, PA0 N,N'-Di-n-butyl-9,9-dimethyl-, PA0 N,N',9,9-Tetra-n-butyl-, PA0 N,N'-Di-n-butyl-9-methyl-9-ethyl-, PA0 N,N'-Di-(cyclopropyl)-methyl-9,9-tetramethylene-, PA0 N,N'-Di-n-hexyl-9,9-dimethyl-, PA0 N,N'-Di-n-hexyl-9-ethyl-9-n-butyl-, PA0 N,N'-Di-n-hexyl-9,9-tetramethylene-, PA0 N,N'-Di-(cyclohexyl)-methyl-9-methyl-9-ethyl-, PA0 N,N'-Di-(cyclohexyl)-methyl-9,9-pentamethylene-, PA0 N,N'-Di-n-decyl-9,9-dimethyl-, PA0 N,N'-Di-isopropyl-9-methyl-9-n-propyl-, PA0 N,N'-Di-n-butyl-9,9-trimethylene-, PA0 N,N'-Di-(2-propenyl)-9,9-dimethyl-, PA0 N,N'-Di-(3-butenyl)-9,9-pentamethylene-, PA0 N,N'-Di-(3-butenyl)-9,9-dimethyl-, PA0 N,N'-Di-(3-butenyl)-9-methyl-9-n-propyl-.
Pharmacological studies of said compounds have been described, for instance, in the following publication: